Contents
Introduction ............................................3 Product Profiles.......................................4 Ethylenediamine (EDA).........................4 Diethylenetriamine (DETA) ..................4 Triethylenetetramine (TETA) ................4 Tetraethylenepentamine (TEPA) ..........4 Heavy Polyamine (HPA) ........................5 Piperazine (PIP)......................................5 Aminoethylpiperazine (AEP) ................5 Aminoethylethanolamine (AEEA) ........5 Typical Physical Properties ....................6 Ethyleneamines Vapor Pressure vs. Temperature ........8 Viscosity vs. Temperature...................9 Specific Gravity vs. Temperature .....10 Ethylenediamine Aqueous Solutions Freezing Point vs. Composition.......11 Vapor-Liquid Equilibria at 760 mm Hg ................................12 Heat of Solution at 22°C ...................13 Specific Gravity vs. Temperature .....14 Piperazine Aqueous Solutions Freezing Point vs. Composition.......15 Vapor-Liquid Equilibria at 760 mm Hg ................................16 Reactions of Ethyleneamines...............17 Reaction Notes ......................................18 Ethyleneamines Applications ..............20 Major End-Uses....................................21 Lubricant and Fuel Additives..............22 Polyamide Resins .................................23 Asphalt Additives and Emulsifiers.......24 Petroleum Production and Refining....24 Resins and Additives for Pulp and Paper .....................................25 Epoxy Curing Agents............................26 Bleach Activators..................................26 Chelates and Chelating Agents...........27 Metal Ore Processing ...........................27 Surfactants and Emulsifiers ................28 Anthelmintics (Dewormers) ...............28 Fabric Softeners....................................29 Fungicides.............................................30 Textiles...................................................31 Polymers and Elastomers....................31 Other Applications ...............................31 Shipping Data........................................32 Product Specifications..........................32 Product Availability...............................33 Storage and Handling ...........................34 Health Effects ........................................35 Ecological Fate and Effects...................36 Product Safety .......................................37 FDA Status .............................................38 References .............................................40 Emergency Service................................47

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Introduction
he Dow Chemical Company, pioneered ethyleneamines development in 1935, when the company was the first to commercialize production, and has been the acknowledged world leader in the business ever since. Today, Dow manufactures ethyleneamines in two world-scale facilities at its Taft, Louisiana, petrochemicals complex. We are the only producer to use both the ethylene dichloride and reductive amination catalytic processes, thus providing unparalleled flexibility in meeting customer needs. Unexcelled quality – in product, technology, and services – is the byword of Dow’s ethyleneamines business. Another first for the company was receipt of ISO 9002 registration in 1990 for the Taft quality systems. Since then, registrations have been received for raw material quality systems, including those for ethylene, ethylene oxide, and ethanolamines, as well as for domestic and international distribution systems. In 1994, our ethyleneamines business won the Shingo Prize for Excellence in Manufacturing. The award recognizes outstanding achievements in manufacturing processes, quality enhancement, productivity improvement, and customer satisfaction. Helping to drive these evergreen quality programs is Dow’s technology leadership. Dedicated research and development focused on the ethyleneamines production processes has constantly improved product quality. Manufacturing technicians employ advanced statistical process control and zone charting for continuous improvement and reduced variability. Backing them is the in-plant laboratory with dedicated equipment for each of the ethyleneamines covered in this publication. And our applications scientists, unsurpassed in their knowledge of ethyl-eneamine end uses, are always ready to assist customers with their needs. Dow’s worldwide distribution network assures you of a readily available source of ethyleneamines.

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Product Profiles
Ethylenediamine (EDA) (1,2-diaminoethane) is the lowest molecular weight
member of the ethyleneamines family. It contains two primary amine groups and forms a maximum boiling azeotrope with water. H2NCH2CH2NH2 EDA is used primarily as an intermediate in the production of bleach activators, fungicides, chelating agents, plastic lubricants, textile resins, polyamides, and fuel additives.

Diethylenetriamine (DETA) is the second linear member of the ethyleneamines
family. It contains two primary and one secondary amine groups. Compared to ethylenediamine, DETA exhibits a broad liquid range: 207°C (405°F) boiling point at 760 mm Hg and -39°C (-38°F) freezing point. H2NCH2CH2NHCH2CH2NH2 DETA is used primarily as an intermediate to manufacture wet-strength paper resins, chelating agents, ion exchange resins, ore processing aids, textile softeners, fuel additives, and corrosion inhibitors.

Triethylenetetramine (TETA) is a liquid containing linear, branched, and cyclic
molecules. The principal tetramine structures are: H2NC2H4NHC2H4NHC2H4NH2 (H2NC2H4)3N HN NC2H4NHC2H4NH2 H2NC2H4N NC2H4NH2 Linear TETA Tris-aminoethylamine (TAEA) Piperazinoethylethylenediamine (PEEDA) Diaminoethylpiperazine (DAEP) (Bis-aminoethylpiperazine)

The major applications of TETA include epoxy curing agents, and the production of polyamides and oil and fuel additives.

Tetraethylenepentamine (TEPA) is a mixture containing linear, branched, and cyclic molecules. The structures of the major TEPA components are:
H2NC2H4NHC2H4NHC2H4NHC2H4NH2 H2NC2H4NHC2H4N(C2H4NH2)2 H2NC2H4NHC2H4N NC2H4NH2 HN NC2H4NHC2H4NHC2H4NH2 Linear TEPA Aminoethyltris-aminoethylamine (AE-TAEA) Aminoethyldiaminoethylpiperazine (AE-DAEP) Aminoethylpiperazinoethylethylenediamine (AE-PEEDA)

Among the major end-uses for TEPA are the preparation of oil and fuel additives, reactive polyamides, epoxy curing agents, and corrosion inhibitors.

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and coatings. The product has two secondary amine groups.Heavy Polyamine (HPA) is a complex mixture of linear. and asphalt additives. Piperazine (PIP) is the simplest cyclic member of the ethyleneamines family. H2NC2H4NHC2H4OH Principal end-uses include surfactants. branched. and one tertiary nitrogen atom. corrosion inhibitors. fabric softeners. and cyclic ethyleneamines. Aminoethylpiperazine (AEP) is unique among the ethyleneamines: it contains one primary. The major end-use applications for HPA include oil and fuel additives. The primary and secondary amine groups. Anhydrous PIP has a fairly high freezing point of 110°C (230°F) and a boiling point of 146°C (295°F) at 760 mm Hg. AEP has a broad liquid range: boiling point of 222°C (432°F) at 760 mm Hg and a freezing point of -17°C (1. Note: “mlm” or “mlm” = –CH 2 CH 2 – 5 . epoxy curing agents. the structures of which can be deduced from the chemistry of manufacture and a knowledge of the structures present in TETA and TEPA. one secondary. HN NH Among the major applications for PIP are anthelmintics. an anhydrous piperazine is available in flake form. Since this narrow liquid range makes it difficult to handle. HN NC2H4NH2 Major end-uses for AEP include the production of urethane catalysts. polyamides. fuel additives. combine the features of an ethyleneamine and an ethanolamine. pharmaceutical preparations. and asphalt additives. chelates. In addition. The structures of the principal components contain six or more nitrogen atoms per molecule. commercial piperazine is often sold in aqueous solutions to facilitate handling and storage. together with the hydroxyl group.4 °F). and as an intermediate for the production of triethylenediamine polyurethane catalyst. Aminoethylethanolamine (AEEA) is an organic base with unique properties that make it an invaluable intermediate.

% by wt 100 100 100(12) 100(12) 100(12) 100(10) 14 100 100 7.030 Ethyleneamine Ethylenediamine Diethylenetriamine Triethylenetetramine Tetraethylenepentamine UHP Heavy Polyamine X Piperazine.32(6) 41 110 .86 0.Typical Physical Properties Apparent Specific Gravity at 20/20°C 0.08 < 0. Anhydrous At 42°C/42°C At 130°C/20°C Pour point Ionization Constant.28 0.15 Freezing Point.72 x 10-4 (2) 0.986 1.65 x 0. 65% Piperazine.015 1.30(1) 275(2) 86.14 129.01 < 0. Anhydrous Aminoethylpiperazine Aminoethylethanolamine (1) (2) (3) (4) (5) (6) Linear component only Typical molecular weight For Piperazine.898 0.43 x 10-4 (3) 0.40 0.01 < 0.22 10.14(3) 86.01 < 0.091 0. Anhydrous Aminoethylpiperazine Aminoethylethanolamine Molecular Weight 60.72 — — (9) (9) Solubility in Water at 20°C.036(4) 0. ˚C 11 .63 x 10-4 10-4 (2) Dielectric Constant at 23°C 13.994 1.13 19.32 8. at 25°C in Water 0.13 Vapor pressure of the solid Extrapolated.43 x 10-4 0.24 0.17 .40 x 0.17 146.29 12.24(1) 189.01 Electrical Conductivity at 25°C.980 0.01 6.46(6) . 65% Piperazine.877(5) 0.10(7) < 0.35 .52 0.73 x 10-4 0.952 0. mm Hg 10.007 0.95 x 10-4 (2) 0.31 x (7) (8) (9) (10) (11) (12) 0. micromhos/cm Ethylenediamine Diethylenetriamine Triethylenetetramine Tetraethylenepentamine UHP Heavy Polyamine X Piperazine.63 10-4 10-4 7.39 .21 104.092 49. with decomposition Solid at this condition At 42°C At 130°C Forms hydrate with time 6 .4(10) — (9) 0.24 9.45(6) Vapor Pressure at 20°C.10 103. K1.

036 0.049 Absolute Viscosity at 20°C.486 (13) (14) (15) (16) At 42°C.3 183 215 279(8) 54 — (9) 10 mm Hg 19. heat of fusion 50.505 1. °C per mm Hg 0.63(14) 0.037 0.0 242.83 cal/g Estimated from vapor pressure using Clausius-Clapeyron equation Calculated from gross heat of combustion 7 .Boiling Point.457 1.139(1) — — .4 88.8 50 mm Hg 47.501 1.0 Refractive Index.9261 .14353 .043 0.65 0.14744 .74 cal/g At 130°C.14487 .73(11) 15.162(1) .52 0. nD20°C 1.16 26.9 144 184 236 27 — (9) ∆ Boiling Point/∆p.304 .056 0. BTU/lb .12395 Heat of Formation at 25°C.58 0. BTU/lb(16) .045 — 0.0 206.1 460.3 100.61 0.058 0.513 — — (9) (9) Specific Heat at 20°C.403 .3 161.6°C.4 140.13251 .1193 1. 750-770 mm.6 134.63 0.8 123. cP 1. cal/g•°C 0.0 83.499 1.052 0. °C 760 mm Hg 117. melting point 109. heat of fusion 72.1 221.483 1.9 277(8) 288(8) — 116 146.14643 . melting point 36°C. BTU/lb(15) 270 197 162 162 99 528 250 152 237 Heat of Combustion at 25°C.13910 .80 7.78(13) 0.14696 .7 22.64 Heat of Vaporization at 760 mm Hg.569 .68 0.256 .5(10) 0.9 127.

Vapor Pressure vs. ˚F 0 1000 800 600 500 400 300 PIP 200 20 40 80 120 160 200 240 320 400 480 560 Vapor Pressure. ˚C 8 . Temperature Temperature.Figure 1: Ethyleneamines. mm Hg 100 80 60 50 40 30 20 10 8 6 5 4 3 2 EDA 65% PIP DETA AEP AEEA TETA TEPA UHP HPA X 1 -20 0 20 40 80 120 160 240 320 Temperature.

cP TETA AEP DETA 10. ˚C 150 200 250 9 . Viscosity vs.0 AEEA TEPA UHP 100.1 -50 0 50 100 Temperature.0 HPA X 1000.0 Viscosity.Figure 2: Ethyleneamines. Temperature 10000.0 EDA 1.0 65% PIP PIP 0.

10 1. t˚C/20˚C 0. Temperature 1.00 AEP TETA DETA Specific Gravity.Figure 3: Ethyleneamines.85 0. Specific Gravity vs.05 AEEA 65% PIP HPA X 1.75 -20 20 60 100 140 180 220 260 Temperature. ˚C 10 .80 0.95 EDA 0.90 TEPA UHP PIP 0.

0˚C -55 0 10 20 30 40 50 60 70 80 90 100 Composition. ˚C -15 -25 -35 -45 Eutectic -53.Figure 4: Ethylenediamine Aqueous Solutions.8˚C -5 Temperature. Weight % Ethylenediamine 11 Composition of Monohydrate Composition of Dihydrate . Composition 15 5 Eutectic -0. Freezing Point vs.

˚C 112 108 104 100 0 10 20 30 40 50 60 70 80 90 100 Composition.Figure 5: Ethylenediamine Aqueous Solutions. Vapor-Liquid Equilibria at 760 mm Hg 120 Vapor Phase 116 Liquid Phase Temperature. Mole % Ethylenediamine 12 .

cal/gm of Solution 30 25 20 15 10 5 0 0 10 20 30 40 50 60 70 80 90 100 Composition. Heat of Solution at 22˚C 50 45 40 35 -∆ Hm. Weight % Water 13 .Figure 6: Ethylenediamine Aqueous Solutions.

90 0.Figure 7: Ethylenediamine Aqueous Solutions.98 0.00 0.94 0.96 Specific Gravity at 20/20˚C 0. Temperature 1.92 0. Specific Gravity vs. Weight % Ethylenediamine 14 .88 0 10 20 30 40 50 60 70 80 90 100 Composition.

Freezing Point vs.Figure 8: Piperazine Aqueous Solutions. Weight % Piperazine Studies show evidence of a metastable freezing point in the region of 20 wt. Composition 120 100 80 Temperature.% piperazine Composition of Hexahydrate 15 . ˚C 60 40 Eutectic 33.2˚C 20 0 Eutectic -1˚C -20 0 10 20 30 40 50 60 70 80 90 100 Composition.

Figure 9: Piperazine Aqueous Solutions. Mole % Piperazine 16 . Vapor-Liquid Equilibria at 760 mm Hg 150 145 140 135 Vapor Phase 130 Temperature. ˚C 125 Liquid Phase 120 115 110 105 100 95 0 10 20 30 40 50 60 70 80 90 100 Composition.

Other ethyleneamines react similarly. depending upon structure.Reactions of Ethyleneamines† † Illustrated by reactions of ethylenediamine (EDA). 17 .

Product distribution is controlled by the ethyleneamine-to-aziridine mole ratio. RX 3. . .Reaction Notes RX 1. Various diamides of EDA are prepared from the appropriate methyl ester or acid at moderate temperatures (2. 18 . .Ureas Ethyleneamines react with urea to form substituted ureas and ammonia (11). . RX 4.Organic Acids Ethyleneamines react with acids. or acyl halides to form amidoamines and polyamides. to form mixtures of hydroxyalkyl derivatives (12-14).3). Product distribution is controlled by the amine-to-epoxide mole ratio. Monoamides can be cyclized to form imidazolines. . water soluble salts. RX 5. forming crystalline. RX 6.Inorganic Acids Ethyleneamines react vigorously with commonly available inorganic acids.Aziridines Aziridines react with ethyleneamines in an analogous fashion to epoxides (15-16).Epoxides Ethyleneamines react readily with epoxides. an explosive compound. This can be done without isolating the monoamide (4-8). is made by reacting one mole of EDA with two moles of nitric acid and splitting two moles of water from the salt at elevated temperatures (1) . Ethylenedinitramine.or liquid-phase reactions of ethyleneamines with glycols in the presence of several different metal oxide catalysts lead to predominantly cyclic ethyleneamine products (18). . RX 7. RX 2. .Alcohols and Alkylene Glycols Simple aliphatic alcohols can be used to alkylate ethyleneamines with hydrogen in the presence of a reductive amination catalyst (17). esters. Either gas. acid anhydrides.Nitriles Hydrogen cyanide (HCN) and aliphatic nitriles (RCN) can be used to form imidazolines (9-10).

is prepared by reacting CS2 in aqueous EDA (22). carbon dioxide. . Ethylene thiourea. the reaction being mildly exothermic. or nitrous acid. such as nitrogen oxides. However.Environmental Reagents: CO2. 19 . O2 Under normal conditions ethyleneamines are considered to be thermally stable molecules. H2O.RX 8. The hydrates of linear TETA and PIP melt around 50°C (25-26). react with ethyleneamines to form mono. crosslinked. Mixing methylene chloride and EDA reportedly causes a runaway reaction (19). activated by electron withdrawing groups. Aliphatic dihalides. NOx. amine hydrates may form. Product distribution is controlled by reactant ratio. a suspect human carcinogen. Reactions of aldehydes with such ethyleneamines as EDA or DETA give mono.and disubstituted imidazolidines via cyclization of the intermediate Schiff base (21). trace levels of byproducts can form and increased color usually results. react with ethyleneamines to form various polymeric.Halides Alkyl halides and aryl halides. metal complexation or choice of solvent. Carbon dioxide reacts readily with EDA in methanol to form crystalline N-(2-aminoethyl)carbamate (23).Sulfur Compounds EDA reacts readily with two moles of carbon disulfide (CS2) in aqueous sodium hydroxide to form bis sodium dithiocarbamate. in concentrated aqueous solutions. However.or disubstituted derivatives. . The products depend on stoichiometry. RX 9. depending on the reactant ratio (20). RX 10. . to form nitrosamine derivatives (24). they are sufficiently reactive that upon exposure to adventitious water. nitrites. which can be reacted with zinc (or manganese) to give the appropriate dithiocarbamate salt. such as ethylene dichloride. RX 11. . nitrogen oxides. and oxygen. water-soluble cationic products or higher ethyleneamine products.Aldehydes Ethyleneamines react exothermically with aliphatic aldehydes. Ethyleneamines are soluble in water. and structure of the ethyleneamine. reaction conditions. N-Alkyl-piperazines and piperazine can react with nitrosating agents.

Ethyleneamines Applications Ethyleneamines are utilized in a wide variety of applications because of their unique combination of reactivity. basicity. . The following table lists the major end-use applications for these versatile materials. They are predominantly used as intermediates in the production of functional products. and surface activity.

Major End-Uses for Ethyleneamines Application Lube Oil Additives Fuel Additives Polyamide Resins Asphalt Chemicals Corrosion Inhibitors Wet-Strength Paper Resins Epoxy Curing Agents Bleach Activators Chelating Agents Ore Flotation Agents Surfactants Fabric Softeners Fungicides Anthelmintics Spandex Fibers Urethanes Military Decontamination Agents Plastic Lubricants Ion Exchange Resins Coatings NOTE: The largest volume applications are indicated by ++ EDA DETA TETA TEPA Ethylenediamine Diethylenetriamine Triethylenetetramine Tetraethylenepentamine HPA PIP AEP AEEA Heavy Polyamine Piperazine Aminoethylpiperazine Aminoethylethanolamine EDA DETA + TETA + + ++ + + ++ TEPA ++ + ++ + + + ++ HPA ++ PIP AEP AEEA ++ ++ + + ++ ++ ++ + + ++ ++ + + ++ + + ++ ++ ++ + + ++ ++ ++ + + ++ + + + ++ ++ + + + ++ 21 .

varnish inhibitors for lubricating oils for twostroke engines (59). all the ethyleneamines have been employed for various products (45).Lubricant and Fuel Additives The largest application area for ethyleneamines is in ashless dispersants for engine oils and other lubricants. normally prepared by the condensation reaction of polyisobutenyl-succinic anhydrides (PIBSAs) (1.and bis-polyisobutenyl-succinimides. and in certain dispersantdetergents for fuels. by solubilizing oil-insoluble liquids. The lubricant additives function mainly to reduce the formation of however. 2) with ethyleneamines (3-44). Post-treatments of the succinimides are commonly utilized for performance improvement in engine oils (4658). Besides the more common means of linking long-chain hydrophobic moieties to ethyleneamines via the succinimide linkage. 22 . and by neutralizing acidic species formed in the combustion process. The higher molecular weight ethyleneamines are most popular for these derivatives. Ethyleneamines are also used in dispersant- sludge and varnish deposits within internal combustion engines by inhibiting the aggregation of particles. They are prepared on a commercial scale by reaction of an alkylphenol with formaldehyde and an ethyleneamine (71-76). The alkyl and ethyleneamine moieties are similar to those used in the succinimide products. The ethyleneamine derivatives most commonly employed for these tasks are the mono. a different linkage is employed in another important class of ashless dispersants – the Mannich bases (60-70).

Thermoplastic polyamides are similarly used in formulating glossy. Anti-rust additives for lubricating oils have also been prepared by reacting ethyleneamines with fatty acids followed by reaction with polyalkylenesuccinic anhydrides (77. is that prepared generally by the condensation reaction of diamines with di. Being soluble in alcohol-based solvents and exhibiting outstanding adhesion to polyolefins. to provide a reaction site. and.and tetramines are sometimes used at low levels to achieve specific performance (2). They are also used to modify alkyd resins in certain thixotropic coating systems (5). and foil webs (8). and as corrosion inhibitors in alkyd paints (7). They are also used in preparing fatty acid/amine soaps and poly(urea) thickeners for lubricating greases. Oil additives providing detergent properties have also been prepared from ethyleneamines (79. Polyamide Resins The main polyamide resin type. 4). abrasionresistant. however. These additives are prepared from ethyleneamines by reaction with various viscosity index improvement polymers that have been modified. 80). Cetane improvement in diesel fuels has been reported for a mixture containing EDA (96). to plasticize nitrocellulose lacquers (6). via chlorination. and paper. 78). polyester. paper. pressure-sensitive. overprint varnishes. Numerous similar products made generally by alkylating or acylating EDA or DETA (87-95) are also used as fuel detergent and deposit control additives. they are particularly suited to these applications. a number of antiwear/antiscuff additives for lube oils and greases also use ethyleneamines. EDA. Dispersant-detergent additives useful in gasoline are prepared by the direct alkylation of ethyleneamines with chlorinated polybutenes (81-86). DETA.and polybasic fatty acids. for example. 23 . and heat-seal adhesives for leather. and AEEA have found significant commercial application as dispersant detergent additives for gasoline when made by this route. Polyamide resins find wide use as binders in printing inks for flexogravure application on certain paper. These polyamides are used in hot-melt. and metal. PIP and certain PIP derivatives are used with EDA in certain cases (3. in addition to the liquid resins used as epoxy hardeners. film. cellophane.Lubricant and Fuel Additives (cont’d) Additives for lubricating oils providing a combination of viscosity index improvement (VII) and dispersancy have also been reported. tri. EDA is a principal amine reactant (1). plastic.

They are usually applied to the petroleum well by any of several methods designed to create a film of inhibitor on the surfaces of the steel structures in the petroleum well. They generally utilize the condensation reaction products of higher ethyleneamines and fatty or dimer acids. as part of a system used to extract thiols from petroleum distillates (18).and bis-amidoamines. and in the processing of certain catalysts (22-25). 24 . demulsifiers. ethyleneamines can be used to decrease the migration of injected chemicals into the formation by adsorption and precipitation (14).and bis-amidoamines. patching.e. as part of a composition used as an antioxidant to control fouling (19). imidazolines. The oil-water emulsions generated at times by petroleum wells can often be broken with certain ethyleneamine derivatives (8-10) (EDA. Similar ethyleneamine derivatives are used to make stable asphalt-in-water emulsions (8-16). They are typically prepared from the higher molecular weight ethyleneamines and fatty acids (1-7). they are represented by the products made from DETA and fatty acids (1-7). and functional additives. to separate alkenes from thermally-cracked petroleum products (20). 13). 11. Petroleum Production and Refining A number of ethyleneamine derivatives are also employed in petroleum production and refining operations as corrosion inhibitors. These films displace the corrosive production fluids and attract a film of petroleum which further isolates the steel from the fluid. Ethyleneamines are also employed in petroleum refining operations. and TETA. mono. neutralizers. mobility. and pH and increase resistance to hydrolysis (15). Specific ethyleneamine derivatives can also be used for water clarification (16. 12. and surfacing.Asphalt Additives and Emulsifiers Mono. Typically. These are generally used as their HCl or acetic acid salts. and their mixtures are used in antistrip formulations and asphalt-in-water emulsions. and polyamides. In some secondary recovery operations. 17). DETA. Corrosion inhibitor formulations for downhole petroleum production applications use a significant volume of ethyleneamines. for example. Antistrip additives promote adhesion between the mineral aggregate and the asphalt in mixtures for road paving. TEPA and other ethyleneamines combined with thickeners help stabilize viscosity. i. imidazolines. to separate carbon disulfide from a pyrolysis fraction (21)..

and/or TEPA in the resin backbone to provide substantivity to the cellulose fibers in paper. The bis-amide made by reacting EDA with stearic acid. Ethyleneamines are also used in the preparation of certain flocculating agents (13). 6. to make nonacidic papers. 11) and polyamines (12). are also used. these types of paper wetstrength resins have been decreasing in popularity due to the adverse health effects associated with formaldehyde. These resins can be used under less corrosive neutral or alkaline conditions. Polyamine wetstrength resins. The most popular paper wet strength resins are the modified polyamides typically made with DETA. ethylenebis(stearamide). The sulfur-free delignification of wood chips with EDA-soda liquors has received some interest in the past few years (22-24).and melamine-formaldehyde types (1. added to the beater stock to improve the wet strength of tissue. and polyamine resins. 27). packaging paper products. toweling. antistatic agents (17-20). adipic acid and epichlorohydrin (37). and acidic conditions required by modified formaldehyde resins. Even though they tend to be less expensive. represent a major end use for ethyleneamines. 25 . 8). is used as a defoamer in paper mill operations. The cationic formaldehyde resins. and paper coatings (21). incorporate ethyleneamines such as DETA. Improved rates of EDA recovery (25) have also been developed for EDA-sulfide pulping processes (26. made by the reaction of ethyleneamines with epichlorohydrin (9). 2).Resins and Additives for Pulp and Paper Ethyleneamine-based chemicals are used widely in the paper industry to impart specific functional characteristics to the finished paper. TETA. both urea. Cationic formaldehyde. rather than the Certain pigment retention and drainage additives made with ethyleneamines include various polyamides (10. Numerous modifications of this resin type have been reported (4. polyamide. waterproofing and sizing compounds (14-16).

to DETA (2) as shown above. and tertiary amino functionality to catalyze that reaction. etc. to give derivatives providing longer pot life and better wetting of glass (14). Most of the amidoamines and reactive polyamides contain significant levels of imidazoline structure. grouts. castings. and a variety of other ethyleneamine modifications (15-18). Mannich bases prepared from a phenol. adhesives. respectively. such as ethylene oxide. cyanoethylation. ketimines. 7). It is prepared by first reacting EDA with two moles of acetic acid to form the bis-amide. and solvent resistance (8). and a polyamine. made by the reaction of EDA with acetone. they are commonly modified in various ways to achieve performance. are widely used for longer pot life and better flexibility. patibility with liquid epoxy resins (9-13).Epoxy Curing Agents All the commercial ethyleneamines are used either neat or as derivatives for curing epoxy resin-based coatings. For example. Bleach Activators Tetraacetylethylenediamine (TAED) has been widely adopted for use in home laundry products as an activator for peroxygen bleaches. laminates. handling. adhesion. and safety improveAmidoamines and reactive polyamides prepared by condensation of TETA or higher polyamines with fatty acids (3-5) and dimer acids (6. Other modifications of the ethyleneamines include partial reaction with epoxy resin to form a prepolymer. 26 . which provides improved com- ments. formaldehyde. (1). Although the ethyleneamines themselves are often used as the curing agent or part of a curing agent package. usually by reaction with acrylonitrile. The presence of different polyamino functionalities in the higher ethyleneamines allows partial reaction with various modifiers while retaining sufficient primary and secondary amino functionality for reaction with the epoxy resin portion of the system. a common modification is the addition of an alkylene oxide. which is then reacted with two moles of acetic anhydride to form the tetra-amide.

polymers (7. made from DETA. Chelating resins. 27 . They operate by forming stoichiometric complexes. AEEA and DETA are also used to make similar polyacetic acid or acetate products. or transported. These same kinds of derivatives can be used for beneficiation of niobium and tantalum ores (3). concentrated. This property makes the ethyleneamines useful in specialized applications. sodium or hydrogen cyanide. Metal Ore Processing Certain processes for enrichment of iron and phosphate ores use amidoamines and imidazolines made from ethyleneamines and fatty acids. They may be made also by reaction of the ethyleneamine with sodium chloroacetate. has found application recently in chlorine-free paper pulp bleaching to prevent iron from decreasing efficiency of the hydrogen peroxide (6). These compounds are produced on an industrial scale primarily through the reaction of the ethyleneamine. or need to be buffered. and formaldehyde in the presence of sodium hydroxide (1. with most di. or separated and hydrolyzed separately (4. It should be pointed out that unmodified ethyleneamines also form stable complexes with certain metal ions.or polyvalent metals. Diethylenetriaminepentaacetate (DETPA). 2). and fibers (9) have also been developed. separated. and in lead ore processing and recovery operations (5-8). These derivatives selectively adhere to silica particles and permit their removal by flotation procedures (1.Chelates and Chelating Agents Polycarboxylic acids and their salts derived from ethyleneamines are used in a variety of applications where specific metal ions interfere with processing. 2). such as zinc and copper. 8). 5). where their metal complexing properties are required. chromium. such as electroplating and electroless metal coating with specific metals and many alloys. made from EDA. The most important commercial family of chelating agents is ethylenediamine tetraacetic acid (EDTA) and its various sodium salts. and as ingredients in systems for etching and for stripping nickel and nickel alloy coatings. and nickel from their sulfide and oxide ores (4). and the ethyleneamines themselves aid extraction of copper. The intermediate polynitrile may either be hydrolyzed in situ (3). called chelates.

The PIP salts have long been the agents of choice for use against roundworms and pinworms (1). A variety of 2-alkylimidazolines and their salts prepared mainly from EDA or AEEA are reported to have good foaming properties (3-8). ethoxylated with an average of 17 moles of ethylene oxide. The imidazolines are generally converted into amphoteric surfactants for this application by reaction with one or two moles of sodium chloroacetate (9-11). Anthelmintics (Dewormers) Piperazine is the active ingredient in certain veterinary anthelmintic preparations – primarily for combating intestinal worms in poultry and swine. 2). elevated temperature to remove two moles of water are all used. AEEA-based imidazolines are also important intermediates for surfactants used in shampoos by TETA. TEPA. amidoamines derived by the non-cyclicizing reaction between amine and acid. amine salts or soaps obtained by simply mixing the amine with a fatty acid (1. The products of a reaction between DETA. 28 . or TEPA and fatty acids also function as water-in-oil or oil-in-water emulsifiers (12). and the imidazoline formed by the reaction under vacuum at virtue of their mildness and good foaming characteristics.Surfactants and Emulsifiers To prepare surfactants derived from ethyleneamines. improves the soil antiredeposition and clay soil removal properties of certain liquid laundry detergents (13).

The amino esters. or to the clothes dryer. such as AEEA. followed by quaternization with dimethyl sulfate. “softer” or more pleasing to the touch. 2). or reacted with ethylene oxide (3) to convert the central secondary amine group to a tertiary amine. made from DETA and fatty acids. Softeners based on bis-imidazoline compounds are also prepared by condensing TETA or TEPA with fatty acids (7) or triglycerides (8). or sodium chloroacetate. Softeners are added to the home washing machine during a rinse cycle or as part of a detergent/softener combination product. as well as their quaternized derivatives. and impart fluffiness.Fabric Softeners Softeners are commonly added to textile materials to make them less harsh. decreased storage stability and performance. that are either cyclized to the corresponding imidazoline by further dehydration. generally with dimethyl sulfate. As a result. to yield compounds that can be formulated into softener products for home laundry use (4-6). which gives amphoteric softeners (9). Softeners also act as antistatic and antisoiling agents. are more subject to hydrolysis than the amidoamine and imidazoline compounds. Softening agents based on DETA and TEPA are also used in industrial textile processing operations (1. Amino esters are made from acids and an amino alcohol. 29 . they have gained some popularity where environmental biodegradation concerns outweigh their The most common ethyleneamine-based fabric softeners are bis-amidoamines. These intermediates are then quaternized.

contact fungicides first used in the early 1940’s. However. it is stabilized by conversion to certain other divalent metal salts. scab. A 2:1 EDA-copper sulfate complex has been suggested for control of aquatic fungi (10). Zineb and maneb are normally formed by the addition of zinc or manganese salts to nabam solutions. preventative. The EBDCs are prepared by reacting EDA with carbon disulfide in the presence of an aqueous base. It is used as the acetate salt for control of apple scab and cherry leaf spot. The ammonium (amobam) and mixed zinc and manganese (mancozeb) salts are also known. and blight. vegetable. The most important of the imidazoline type (8) is 2-heptadecyl-2-imidS CH2–NH–C–S–Na H2C–CH2–CH2–NH2 + CS2 + 2NaOH CH2–NH–C–S–Na S + 2 H2O This sodium derivative. nabam. 30 . and grain crops for prevention of mildew. rust. potato.Fungicides The ethylenebisdithiocarbamates (EBDCs) are a class of broad-spectrum. The zinc (zineb) and manganese salts (maneb) are especially effective (1-7) and are today the azoline (9). Other materials based on EDA have also been suggested as fungicides. prepared from EDA and stearic acid. They are used on many fruit. primary commercial products. was found to be unstable.

petroleum production. stone and concrete coatings. explosives. to reduce static in polystyrene foam. EDA reacted with stearic acid makes ethylene-bis(stearamide) (EBS) that is used as an external lubricant for ABS resin and PVC. The bisamidoamine condensate made from TETA or TEPA and stearic acid is used as a defoamer in certain textile treatment baths. in phenolic resin curing. gas and water treating. ion exchange resins. and as a parting material. catalysts (TEDA [triethylenediamine] is a significant example). 2). Dye assist compounds for synthetic fibers have been derived from EDA. viscosity regulator. fire retardants.Textiles Ethyleneamines are used in the textile-related industries for a variety of applications. Acrylate and other monomer vapors can be efficiently removed from vent streams with scrubber solvents containing TETA. and mothproofing (7). light stabilization of spandex fibers (4). to inhibit isoprene polymerization. and they are used in styrene-butadiene latex processes to coagulate the low levels of finely-dispersed particles in the reaction medium (12-15). DETA. preservative. TETA has been recommended as a curing agent for furfural resin binders in foundry molds and molded graphite. polymer concrete and concrete additives. Ethyleneamines find application in vulcanization processes for certain rubbers (1-11). DETA is a component of Nylon 6 (11). and membranes. EDA is used in preparing silane and silanol compounds that improve the adhesion between inorganic surfaces and polymer films. Polymers and Elastomers EDA is a key component of the polymer in spandex fiber. plaster systems. functional fluids. They include coal-oil emulsification and coal extraction. 31 . TETA. static prevention (6). including the treatment of a wide variety of natural and synthetic fibers for modification of certain properties (1. shrinkproofing wool (5). EDA specifically can be used as a stabilizer for certain urea resins. Urethane systems and processes employ certain ethyleneamines and their derivatives as curing agents. and polyol starters. and for etching polyimide films. as precursors for certain compounds providing durable press (3). and surface gloss enhancer. Other Applications Ethyleneamines find application in numerous other specific industries. pharmaceuticals. and TEPA (8-10). industrial corrosion inhibition. ceramics.

995 1.984 1.48 7. Anhydrous Aminoethylpiperazine Aminoethylethanolamine (1) At 65°C (2) Solid at this condition (3) At 20°C to 30°C (4) At 45°C to 65°C at 20°C 7.027 (5) At 80 °C at 15.953 0.987 1. 65% Piperazine.60 Metric Units Average Weight per liter.44 8.980 0.95 8.015 — (2) — (2) 0.56°C 7.56°C 0. 32 .900 0. additional information on shipping data.21 8.011 1. labeling and container requirements may be obtained by contacting Dow at the numbers on the back of this booklet. 65% Piperazine.991 1.27 8.39 (1) — (2) 8.30 8. kg Ethyleneamine Ethylenediamine Diethylenetriamine Triethylenetetramine Tetraethylenepentamine UHP Heavy Polyamine X Piperazine. Please contact Dow at the numbers on the back of this booklet.47 — (2) — (2) 8.031 Product Specifications Product specifications and methods are available upon request.005 (1) — (2) 0.24 8. Anhydrous Aminoethylpiperazine Aminoethylethanolamine (1) At 65°C (2) Solid at this condition (3) At 20°C to 30°C (4) At 45°C to 65°C at 20°C 0.51 7.15 8. lb Ethyleneamine Ethylenediamine Diethylenetriamine Triethylenetetramine Tetraethylenepentamine UHP Heavy Polyamine X Piperazine.92 8.896 0.Shipping Data Since governmental regulations are subject to change.18 8.949 0.57 (5) At 80 °C at 15. We will provide a technical contact to discuss specific questions you might have. Average Weight per gallon.977 0.

00076 — (2) — (2) 0.00110 0.00076 — (2) — (2) 0. ASTM Method D 92 TO = Tag Open Cup.000769 (3) 0.00092 0.00680 (3) 0.00076 0.00640 (3) Coefficient of Expansion. ASTM Method D 92 TO = Tag Open Cup.000951 0.000943 (4) — (2) 0.00106 0.00086 0.000747 (3) 0. ASTM Method D 93 C = Cleveland Open Cup.00077 at 55°C 0.00077 Flash Point (6).00077 at 55°C 0.00110 0.00083 0.00077 Flash Point (6).00787 (4) — (2) 0.00081 0. tank truck.00642 (3) 0.00076 0.000815 (3) 0.00081 0. ASTM Method D 1310 Product Availability Products are available in bulk ocean tanker.00623 (3) 0. °F Closed Cup 110 T 208 P 300 P 340 P 345 P None T 130 P 215 P 260 P Open Cup 103 TO 225 C 310 C 360 C 445 C 205 C 215 C 250 C 310 C (6) T = Tag Closed Cup.∆lb/gal/∆t 10°C to 30°C.00085 0.000767 (3) Coefficient of Expansion.00089 0.00095 (5) — (2) 0. per °C 0.00080 0.00095 (5) — (2) 0.00092 0. ASTM Method D 56 P = Pensky-Martens Closed Cup.00086 0.000842 0.00080 0.000792 0. ASTM Method D 1310 ∆kg/liter/∆t 10°C to 30°C. per °C 0.00703 0. 33 . rail car.00081 0. per °C at 20°C 0.00085 0. °C Closed Cup 43 T 98 P 149 P 171 P 174 P None T 54 P 102 P 127 P Open Cup 39 TO 107 C 154 C 182 C 229 C 96 C 102 C 121 C 154 C (6) T = Tag Closed Cup.00661 0. ASTM Method D 93 C = Cleveland Open Cup.00794 0.00106 0. per °C at 20°C 0.00089 0. and nominal 55gallon drums.00083 0. ASTM Method D 56 P = Pensky-Martens Closed Cup.00081 0.

Closed cellular glass insulation is normally resistant to insulation fires because it is difficult for the ethyleneamines to saturate these materials and also difficult for air to contact the product. Proper selection of materials of construction for ethyleneamine service is essential to ensure the integrity of the handling system and to maintain product quality. then 300 series stainless steels are recommended for the storage tanks. and either smoldering or a flame may be observed. Carbon steel transfer lines or agitated equipment will suffer enhanced corrosion because of erosion of the passive film by the product velocity. since TFE is not a true elastomer. e. watersaturated containers. Carbon steel with baked phenolic lining is acceptable for storage of many pure ethyleneamines. or be thoroughly wetted with water and then disposed of in closed. Storage under a dry. sometimes rapidly and usually exothermically. but the products will pick up iron and discolor badly. dedicated processing equipment is recommended. transfer lines. Galvanized steel. valves. Risk of insulation fires can be reduced by insisting on good housekeeping. Most commonly used industrial thermal insulating materials are acceptable for ethyleneamine service.Storage and Handling Ethyleneamines react with many other chemicals. TFE is an alternative to elastomers since it is resistant to ethyleneamines. even at ambient temperature. However. A 300 series stainless steel is often specified for pumps. heavier ethyleneamines without noticeable impact on product quality. or AEEA storage tanks. and oxygen from the atmosphere may be absorbed by the amines.. 34 . However.001 in/yr) at typical storage temperatures. except EDA. Recommended gaskets for ethyleneamine service are made of GRAFOIL™ flexible graphite or polytetrafluoroethylene (TFE). Water. However. nitrogen oxides. and training personnel. it may not always prove suitable as a replacement material. Nonmetallic equipment is not normally used for ethyleneamine service. like many other combustible liquids. If this cannot be tolerated. this may lead to spontaneous combustion. minimizing insulated flanges and fittings. consistent with local and federal regulations. in dedicated service. any of these media contaminated with ethyleneamines should be washed with water to remove the amines. inert atmosphere (such as low CO2-containing nitrogen) will minimize this sort of degradation.g. Modest storage temperature (less than 60°C) and nitrogen blankets will allow the use of carbon steel. DETA. porous insulation may introduce the hazard of spontaneous combustion if the insulation is saturated with ethyleneamines from a leak or external spill. Corrosion is not extreme (<0. dumped filter cake. Carbon steel is not recommended for EDA. Also. for nonaqueous. certain grades of these materials may be acceptable in some storage applications. self-heating of ethyleneamines may occur by slow oxidation in other absorbent or high-surface-area media. No single elastomer is acceptable for the entire product line. This may lead to low levels of byproducts and increase the color of the product. carbon dioxide. heating coils. To avoid this situation. maintenance of weather barriers. and small agitated tanks. spill absorbents and metal wire mesh (such as that used in vapor mist eliminators). Ethyleneamines can permeate polyethylene and polypropylene. Consequently. In some cases. copper and copper-bearing alloys are unacceptable for all ethyleneamine service.

as well as recommended safety procedures. Hydrate problems are usually avoided by insulating and heat tracing equipment to maintain a temperature of at least 50°C. may be found in the Material Safety Data Sheets. In addition. which causes the carbamates to decompose. EDA has the lowest flash point (Tag Closed Cup): 43°C (110°F). Tank vents and safety devices are also susceptible to fouling by solid amine carbamates formed by the reaction of the amines with carbon dioxide. Storage at elevated temperatures can cause vapors “breathing” from the tank to contain significant concentrations of product. mineral acids contamination). ethyleneamines exhibit good temperature stability. contact Dow at the numbers on the back of this booklet. Additionally. in certain concentrations.The amines do not present any unusual flammability problem at ordinary temperatures. This information is of a general nature. vent lines and safety devices. vent units and relief devices may be steam-traced to maintain 160°C. Vent fouling can be reduced by using nitrogen blankets on storage tanks to exclude atmospheric CO2. Warm water cleanup can reduce the extent of the problem. although the amines are water-soluble. Water cleanup of ethyleneamine equipment can result in hydrate problems. heavier ethyleneamines may be stored at elevated temperatures (40-60°C) to ease inplant handling by lowering the viscosity. solid amine hydrates may form. Hydrates can plug processing equipment. Ethyleneamines are typically maintained above their freezing points which may require storage above ambient temperatures (particularly EDA and PIP). Testing for thermal stability is suggested whenever ethyleneamines are mixed with other materials. As commercially pure materials. For the latest Material Safety Data Sheets on ethyleneamines. contact Dow at the numbers on the back of this booklet and request our Ethyleneamines Storage and Handling Brochure and/or a technical contact who will discuss specific questions about acceptable materials of construction and storage practices. which are updated as new information becomes available. This degradation increases in rate as the temperature and/or time increases. even in areas where routine processing is nonaqueous. At elevated temperatures some product breakdown may be observed in the form of ammonia and the formation of lower and higher molecular weight species. For additional information. which can be a nuisance in handling. All amine vents should be routed to a safe location and “smoking vents” routed to water scrubbers to capture the vapors. Health Effects Information on health effects and their management. contaminants can lower the onset of rapid exothermic thermal decomposition (for example. Also. 35 . Additionally. Vent units require periodic inspection to verify that fouling is not occurring and to ensure that seals are functioning properly to exclude air from the tank.

with the exception of EDA/DETA studies which used acclimated seed. Bacterial inhibition tests indicate that none of these amines tested should be inhibitory to conventional wastewater treatment processes at expected discharge levels of less than 500 mg/L. The impact of acclimation on the rate and extent of biodegradation is shown by the EDA and DETA acclimated seed data. Calculated value based on oxygen required to oxidize the chemical to carbon dioxide and water. ASTM. while the nitrogen converts to and remains as ammonia.68 1.13 1. and 20. Ecological Fate and Effects of Ethyleneamines Theoretical Oxygen Demand.28 1.50 1.48 1. and Standard Methods techniques.63 Calc.86 1.69 — 1. 65% Aminoethylpiperazine Aminoethylethanolamine Carbonaceous Meas. 17th ed.33 1. EDA. These studies were conducted by procedures which follow the EPA. Several amines. showed more toxicity to Daphnia magna with LC50 values ranging from 5 to 40 mg/L. Natural acclimation in a wastewater treatment plant or in the general environment would be expected to increase the rate and extent of biodegradation for the related compounds. Aquatic toxicity measurements showed only moderate toxicity for most of the tested amines. 36 . (1989). Nonacclimated domestic sewage microorganisms used as seed.54 Nitrogenous Calc. The biooxidation values are calculated as percentage ratio of BOD and ThOD (BOD/ThOD x 100). 10. which rapidly biodegraded. Public Health Assoc.23 (1) Measured by Chemical Oxygen Demand (COD) procedure published in Standard Methods for the Examination of Water and Wastewater.86 1.88 1..86 1. The data presented in the following table show that the amines biodegrade slowly.64 1.49 1. The nitrogenous oxygen demand is calculated based on nitrogen being oxidized to nitrate by nitrifying bacteria.84 1. and AEP. (2) Measured in dilution bottle biochemical oxygen demand test published in Standard Methods. (COD) 1. 1. except for EDA and AEEA.93 1.Ecological Fate and Effects Dow has conducted a series of laboratory studies on the biodegradation and ecological effects of these amines. (3) The measured biooxidation as a percent of the total carbonaceous and nitrogenous oxygen demand (sum of calculated carbonaceous and nitrogenous ThOD values) is presented for Days 5. DETA. 2. TETA.75 — — 1.94 1. Biodegradation was measured by the riversimulating 20-day biochemical oxygen demand (BOD) test using nonacclimated microorganisms.55 1. (ThOD) mg/mg(1) Product Evaluated Ethylenediamine Diethylenetriamine Triethylenetetramine Tetraethylenepentamine UHP Heavy Polyamine X Piperazine.

or cosmetic. The 95% confidence limits (95% CL) are shown in parentheses. The customer should furnish the information in these publications to its employees. or in a product or process in which it may contact a food. contractors. or cosmetic until the user has determined the suitability and legality of the use. or any other users of the product(s). mg/L Aquatic Toxicity (5) LC50. medical device. Since government regulations and use conditions are subject to change. and comply with the information contained in this publication and the current Material Safety Data Sheet(s).Product Safety When considering the use of any Dow products in a particular application. Biochemical Oxygen Demand(2). it is the user’s responsibility to determine that this information is appropriate and suitable under current. Dow requests that the customer read. understand. 37 . For Material Safety Data Sheets and other product safety information. Before handling any other products mentioned in the text. No chemical should be used as or in a food. applicable laws and regulations. and customers. (5) Fathead minnows and Daphnia magna bioassays were conducted using procedures published by EPA and ASTM. drug. medical device. contact Dow at the numbers on the back of this booklet. you should review our latest Material Safety Data Sheets and ensure that the use you intend can be accomplished safely. drug. % biooxidation Total Carbonaceous(2) Days 5/10/20 68/100/100 A36(6)/A45(6)/A70(6) <5/<5/<5 A23(6)/A46(6)/A70(6) 3/4/9 4/7/12 <5/<5/<5 <10/<10/<10 2/4/7 2/64/90 —/—/— —/—/— —/—/— —/—/— —/—/— —/—/— 1/37/53 >5000 680 — — 4600 1400 >5000 25/37/78 1000 Nitrogenous(3) Days 5/10/20 Bacterial (4) Inhibition IC50. you should obtain available product safety information and take necessary steps to ensure safety of use. (6) Biooxidation values for EDA and DETA are taken from tests with acclimated microorganisms. No nitrification was measured in the acclimated systems. mg/L 48-hour 96-hour Daphnia magna Fathead Minnow 5 (4-6) 17 (15-19) 40 (35-50) — — 90 (80-110) 36 (25-50) 110 (90-130) 210 (190-230) 260 (220-310) 330 (280-400) 310 — 720 (640-800) 560 (500-620) 515 (470-560) (4) Determined by turbidity/growth procedures where the median inhibition concentration (IC50) is measured after 16 hours of incubation with sewage microorganisms. and request that t hey do the same.

210 176.0 ppm based on the weight of raw cane or beets processed. Component in an antimicrobial formulation used in cane sugar mills.5 wt% of the rubber product.300 175. Polyamides from vegetable oil acids and sebacic acid for use in side seam and can-end cements. applied to the sugar mill grinding. and/or diffusor systems at a maximum level of 2. as a modifier for melamine-formaldehyde resins used in cellophane.390 176. Modifier for urea-formaldehyde resins for use as the basic polymer in cellophane and as a resin to anchor coatings to substrate. and/or diffusor systems at a maximum level of 1. Component in an antimicrobial formulation used in cane sugar and beet sugar mills. However.2600 178.1200 177.320 173. aqueous. not to exceed 1. Modifier for amino resins used as a component of the coated and uncoated food-contact surface of paper and paperboard in contact with fatty. Urea-formaldehyde resins chemically modified with polyamines made by reacting ethylenediamine with dichloroethane or dichloropropane for use as a component of the coated or uncoated food-contact surface of paper and paperboard in contact with dry food.105 175. Polyamides from dimerized vegetable oils for use as adjuncts for epoxy resins.380 175.180 176. aqueous. sulfanilic acid. Modifier for melamine-formaldehyde resins for use as the basic polymer in cellophane.25 173.180 176. crusher. at a level not to exceed 0.4’-iso-propylidenediphenol epichlorohydrin epoxy resins.320 175.1200 177.170 176.5 wt% based on the monomers. it is the responsibility of the user of an ethyleneamine as a Direct or Indirect Food Additive to read and understand any applicable FDA regulations in Title 21 of the Code of FDA Regulation Ethylenediamine 21 CFR Permitted Uses 173. applied to the sugar mill grinding. and dry food. aqueous. Polyamines made by reacting ethylenediamine with dichloroethane or dichloropropane. crusher.180 176. Catalyst and crosslinking agent for epoxy resins used in resinous and polymeric coatings applied as a continuous film or enamel over a metal substrate or applied as a continuous film or enamel to any suitable substrate provided that the coating serves as a functional barrier between the food and the substrate and is intended for repeated food-contact use. and dry food.300 175. Catalyst for epoxy resins and component of polyamides for use in zinc-silicon dioxide matrix coatings.180 176.300 177.3120 38 . Accelerator in vulcanization of rubber articles intended for repeated use. Catalyst activator in semirigid and rigid acrylic and modified acrylic plastics. Catalyst for epoxy resins and component of polyamides for use in xylene-formaldehyde resins condensed with 4.105 175.170 176. Component of the coated or uncoated food-contact surface of paper and paperboard in contact with dry food (as a crosslinking agent in polymerization).1200 177. and other listed amines.170 176. and as a resin to anchor coatings to substrate. Polyamines made by reacting ethylenediamine with dichloroethane or dichloropropane for modifying urea-formaldehyde resins used as the basic polymer and as a resin to anchor coatings to the substrate in the manufacture of food-packaging cellophane. Component of adhesives used in articles intended for packaging.FDA Status Dow provides the following FDA Status Summary for the convenience of our customers.1210 177.1010 177. Adjuvant in the preparation of slimicides used as antimicrobial agents to control slime in the manufacture of paper and paperboard.180 176. Polyamides formed by reaction with dimerized vegetable oil acids for use as components of food-packaging adhesives.300 175.170 176. or holding food. and dry food.180 176. Crosslinker with epichlorohydrin to make ion-exchange resins used in the processing of food. Additive in the production of animal glue. Modifier for urea-formaldehyde and melamine-formaldehyde resins for use as a component of the coated or uncoated food-contact surface of paper and paperboard in contact with fatty. Catalyst for epoxy resins used as the food contact surface of paper and paperboard in contact with fatty. Formulation of defoaming agents used in the manufacture of paper and paperboard prior to and during the sheet forming operation. transporting. Polyamide-epichlorohydrin resins prepared by reacting adipic acid or other acids with diethylenetriamine to form a basic polyamide and further reaction of the polyamide with other materials to form water-soluble thermosetting resins for use in the manufacture of paper and paperboard. 175.1200 177. Modifier for urea-formaldehyde and melamine-formaldehyde resins used as the basic polymer in resinous and polymeric coatings on a metal substrate.300 Preparation of ion-exchange membranes used in the processing of grapefruit juice. Catalyst for epoxy resins and component of polyamides for use in making closures with sealing gaskets.0 ppm based on the weight of raw cane processed.20 173.

Furthermore. Diethylenetriamine (EDA) Triethylenetetramine (DETA) ✔ ✔ Tetraethylenepentamine (TETA) ✔ Aminoethylethanolamine (TEPA) ✔ (AEEA) ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ 39 . safe. it is the responsibility of the user to determine that any such use is suitable.Federal Regulations (21 CFR) to determine any limitations or restrictions on the proposed use. and FDA-compliant.

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